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12. Digable Planets

Major Hit: "The Rebirth of Slick (Cool Like Dat)" (1992)

Other Hit: "Where I'm From" (1993)

Digable Planets were one of the more adventurous rap groups of the early '90s. While other acts were content to just sample from jazz records, DP actually sounded like they were cut from be-bop cloth. In a sense, the song title was saying, they represented the rebirth of "cool." And they largely pulled it off—for a while anyway. Although their mainstream buzz inevitably died down, DP continued to put up hits like "Where I'm From." (By the way, the artist formerly known as Butterfly is still in the game with his group Shabazz Palaces.)